Трехкомпонентной конденсацией 2-нафтиламина или 1,5-диаминонафталина, замещенных бензальдегидов и циклопентан-1,3-диона в одну стадию через промежуточное образование неустойчивого ариламинокетоенола в результате отщепления молекулы воды и дальнейшей гетероциклизации получен ряд новых 11-(R'-фенил)-8,9-дигидро-7H-бензо[f]циклопента[b]хинолин-10(11H)-онов и 7,14-бис(И-фенил)-2,3,9,10,11,14-гексагидроциклопента[2,3]хинолин[8,7-h]циклопента[b]хинолин- 1,8(4Н,7Н)-дионов.

A series of new 11-(R-phenyl)-8,9-dihydro-7H-benzo[f]cyclopenta[b]quinolin-10(11H)-ones and 7,14-bis(R-phenyl)-2,3,9,10,11,14-hexahydrocyclopenta[2,3]quinolino[8,7-h]cyclopenta[b]quinoline-1,8(4H,7H)-diones were synthesized by three-component condensation of naphthalen-2-amine or naphthalene- 1,5-diamine with substituted benzaldehydes and cyclopentane-1,3-dione in one step through intermediate formation of unstable arylaminoketoenol.

Octahydroacridino[4,3-c]acridine-1,9(2H,5H)dione derivatives were synthesized via condensation of bisazomethines (N 1 ,N 5 -di-R-benzylidenenaphthalene-1,5-diamines) with dimedone in butanol-1. The structures of the prepared compounds were confirmed using NMR and IR spectroscopy. Studies of the spectral and luminescent properties of the synthesized compounds in EtOH and DMF at 293 and 77 K showed that the absorption spectra were composed of three electronic transitions S n ← S 0 (n = 1–3) with frequencies of 24,400 and 20,800 cm–1 for the 0–0-transitions from the singlet (S 1 ) and triplet (T 1 ) states, respectively. Fluorescence quenching by EtOH was due to the formation of an H-bonded complex, the lifetime of which was <10 –9 s. The naphthalene fragment in the molecule was responsible for phosphorescence in the studied compounds.

Derivatives of octahydroacridino[4,3-c]acridin-1,9(2H,5H)dione are synthesized using the condensation of diazomethines (N 1 ,N 5 -di-R-benzylidenenaphthalen-1,5-diamines) with dimedone in butanol. The structure of the prepared compounds is confirmed by the methods of nuclear magnetic resonance and IRspectroscopy. The spectral and luminescent properties of the synthesized compounds are studied in ethanol and DMF as solvents at 293 and 77 K. It is found that the absorption spectra are formed by three S n ←S 0 (n = 1-3) electronic transitions and the frequencies of 0-0 transitions from singlet (S 1 ) and triplet (T 1 ) states are equal to 24400 and 20800 cm - 1 , respectively. The fluorescence quenching by ethanol is due to the formation of the complex with the hydrogen bonds; the lifetime of this complex is less than 10 - 9 s. Phosphorescence in the studied compounds is caused by the existence of a naphthalenic fragment in the molecule.

Condensation of 2-naphthylamine, aromatic aldehydes, and dimedone was found to produce 9,10-dihydrobenzo[a] acridin-11-one derivatives according to PMR, 13C NMR, and IR spectroscopy and mass spectrometry. Correlation spectroscopy showed that the carbonyl in the synthesized dihydrobenzoacridinone derivatives was located on C11.

A number of new acridino[4,3-c]acridinedione derivatives have been synthesized for the first time by condensation of N (1),N (5)-bis(arylmethylidene)naphthalene-1,5-diamines with cyclic 1,3-diketones (cyclohexane-1,3-dione and dimedone). The product structure has been determined by two-dimensional NMR spectroscopy, and a probable reaction mechanism has been proposed.

N-containing derivatives that were promising as biologically active compounds were synthesized via a series of transformations of the monoterpenoid pulegone isolated from Ziziphora clinopodioides essential oil.

9,9-Dimethyl-12-[(5-aryl-2-furyl) (or 5-aryl-2-thienyl, or 5-aryl-1-methyl-1H-pyrrolyl)]-7,8,9,10,11,12-hexahydrobenzo[a]acridin-11-ones were synthesized, and their absorption and luminescence spectrum characteristics in ethanol at room temperature and at 77 K were studied. The spectra suggest the existence of these compounds in a liquid solution as mixtures of conformers, each of which is characterized by its own absorption and fluorescence spectra.

Three-component condensation of naphthalen-2-amine with 5-arylfuran(thiophene, N -methylpyrrole)-2-carbaldehyde and 5,5-dimethylcyclohexane-1,3-dione, as well as condensation of N -[(5-arylfuran(thiophen)-2-ylmethylidene]naphthalen-2-amine with 5,5-dimethylcyclohexane-1,3-dione gave the corresponding 12-[5-arylfuran(thiophen, N -methylpyrrol)-2-yl]-7,8,9,10-tetradrobenzo[ a ]acridin-11(12 H )-ones.

By a three-component condensation of 8-aminoquinoline, aromatic aldehydes, and 1,3-diketones accompanied by the Hofmann-Martius rearrangement hydrobenzophenanthroline derivatives were synthesized. Their spectral and luminescence properties in ethanol solution were investigated at 293 and 77 K.

Hydrobenzophenanthrolinone derivatives were synthesized by three-component condensation of 8-aminoquinoline, aromatic aldehydes, and dimedone. The structures of the obtained substances were confirmed by NMR and IR spectroscopy and mass spectrometry. Spectral-luminescent investigations of the synthesized compounds showed that they were characterized by high oscillator strengths for allowed electronic transitions S n ← S 0 (n = 1–3). Low fluorescence quantum yields in EtOH (Φfl ~ 10–4–10–3) and an increase of the Φfl values in toluene (~10–2) at room temperature and with lowering the temperature to 77 K (Φfl ~ 10–1) for a number of the compounds under study were satisfactorily explained within the framework of Marcus theory.

Compounds that were promising as fragrances were prepared by a series of transformations at the carbonyl group of 7-methyl-2H-benzo[b][1,5]dioxepin-3(4H)-one.

The three-component condensation of 1- or 2-naphthylamines, aromatic aldehydes, and methyl 2-(benzo[1,3]dioxol-5-yl)-4,6-dioxocyclohexane-1-carboxylate led to the formation of methyl 9-( cis,trans )-10-(1,3-benzodioxol-5-yl)-7-aryl-8-oxo-7,8,9,10,11,12-hexahydrobenzo[c]acridine-9-carboxylates or methyl 10-( cis,trans )-9-(1,3-benzodioxol-5-yl)-12-aryl-11-oxo-7,8,9,10,11,12-hexahydrobenzo[a]acridine-10-carboxylates. The spectral luminescence properties of compounds obtained were investigated in ethanol at 293 and 77 K.

A three-component condensation of 2-naphthylamine, aromatic aldehydes, and methyl 2,2-dimethyl-4,6-dioxocyclohexanecarboxylate afforded methyl ( cis,trans )-12-aryl-9,9-dimethyl-11-oxo-7,8,9,10,11,12-hexahydrobenzo[ a ]acridine-10-carboxylates. Spectral luminescence and nonlinear optical properties of compounds obtained were investigated.

Reactions of azomethines (Schiff bases) prepared from vanillin and vanillal ethers and 1-naphthylamine with cyclohexane-1,3-dione in butanol afforded in 40–64% yields 7-[4-alkoxy-3-methoxy(hydroxy)phenyl]-10,11-dihydrobenzo[c]acridin-8(7H,9H,12H)-ones and 4-(8-oxo-7,8,9,10,11,12-hexahydrobenzo[C]acridin-7-yl)-2-methoxy(ethoxy)phenyl esters of carboxylic acids. The reaction products presumably formed by the rearrangement of the azomethine adduct with the cyclohexane-1,3-dione proceeding by the type of Hofmann-Martius rearrangement. The structure of compounds synthesized was confirmed by the elemental analysis, UV, IR, and 1H NMR spectra.

5-Aryl-1-methyl-1,2,3,4-tetrahydrobenzo[ a ]phenanthridines were synthesized by cascade heterocyclization of the corresponding substituted benzaldehydes with 2-methylcyclohexanone and naphthalen-2-amine in a polar solvent in the presence of hydrochloric acid.

By Knoevenagel condensation and by three-component condensation 3-arylmethylenetetrahydrofuran-2,4-diones and previously unknown 8,11-dihydro-11-arylbenzo[ f ]furo[3,4- b ]quinolin-10(7 H )-ones were respectively synthesized. The luminescent spectra and nonlinear-optical characteristics of compounds obtained were investigated.